Dimethyl Sulfoxide → HCID 18187475, Verbindung
Reaktionsgleichung
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]([OH:31])[CH:25]([CH3:30])[C:26](=[O:29])[CH2:27][CH3:28])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:31])[CH:25]([CH3:30])[C:26](=[O:29])[CH2:27][CH3:28])[CH2:20][CH2:19]1)=[O:17])([CH3:13])([CH3:12])[CH3:14]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of oxalyl chloride (0.34 mL, 3.9 mmol) in methylene chloride (12 mL) at −78° C. was treated with DMSO (0.43 mL, 6.0 mmol) and the resulting mixture was stirred cold for 10 min. A solution of 1-(t-butoxycarbonyl)-4-(1-(RS)-hydroxy-2-(RS)-methyl-3-oxopent-1-yl)piperidine (514 mg, 1.7 mmol) (from Step C) was added and the resulting solution was stirred cold for 1 h. N,N-Diisopropylethylamine (2.4 mL, 13.7 mmol) was added and the resulting mixture was warmed to 0° C. The reaction was quenched with 1.0 N HCl (25 mL) and extracted with ether (100 mL). The extract was dried over magnesium sulfate and concentrated. MPLC (Biotage) on a 40 S silica cartridge using 2:1 v/v hexanes/ethyl acetate as the eluent afforded 435 mg (85%) of the title compound.
Aufarbeitung
- stirringthe resulting solution was stirred cold for 1 h
- customThe reaction was quenched with 1.0 N HCl (25 mL)
- extractionextracted with ether (100 mL)
- dry with materialThe extract was dried over magnesium sulfate
- concentrationconcentrated
Quellen und Nachweise
- ORD-Eintrag
- ord-beb450785fd84a879bd2d246b9410e64
- Quelldatensatz
- uspto-grants-2002_08
- Patentnummer
- US06432981B1
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